Chicago (MDW) to Montego Bay (MBJ), Feb 26, 2027: round trips from $397, one way from $185

Chicago (MDW) to Montego Bay (MBJ), Feb 26, 2027: round trips from $397, one way from $185 on Axel, checked Nov 13, 2026. Lowest published fares: $397 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Feb 26–28, 2027; $185 one way, Axel-exclusive, Frontier Airlines, 1 stop, Feb 26, 2027; 1 adult, economy, checked Nov 13, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

Exact travel dates Airline Flights Times, duration, stops Total price Price checked
2027-02-26 · one way Frontier Airlines F92292 + F9125 06:08:00→15:29:00 8h 21m 1 stop via ATL Axel-exclusive $185 Nov 13, 2026
2027-02-26 · one way Southwest Airlines WN2964 + WN292 06:35:00→14:45:00 7h 10m 1 stop via MCO Axel-exclusive $237 Nov 13, 2026
2027-02-26 → 2027-02-27 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→15:29:00 8h 21m 1 stop via ATL · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $417 Nov 13, 2026
2027-02-26 → 2027-02-27 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→14:45:00 7h 10m 1 stop via MCO · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $464 Nov 13, 2026
2027-02-26 → 2027-02-28 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $397 Nov 13, 2026
2027-02-26 → 2027-02-28 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $443 Nov 13, 2026
2027-02-26 → 2027-03-01 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-01 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-02 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-02 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-03 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-03 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-04 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-04 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-05 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-05 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-06 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN1043 06:08:00→15:29:00 8h 21m 1 stop via ATL · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $429 Nov 13, 2026
2027-02-26 → 2027-03-06 Southwest Airlines WN2964 + WN292 / WN1043 06:35:00→14:45:00 7h 10m 1 stop via MCO · 14:25:00→17:35:00 4h 10m nonstop Axel-exclusive $475 Nov 13, 2026
2027-02-26 → 2027-03-07 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-07 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-08 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-08 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-09 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-09 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-10 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-10 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-11 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-11 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026
2027-02-26 → 2027-03-12 Frontier Airlines / Southwest Airlines F92292 + F9125 / WN293 + WN2595 06:08:00→15:29:00 8h 21m 1 stop via ATL · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $407 Nov 13, 2026
2027-02-26 → 2027-03-12 Southwest Airlines WN2964 + WN292 / WN293 + WN2595 06:35:00→14:45:00 7h 10m 1 stop via MCO · 15:45:00→23:00:00 8h 15m 1 stop via MCO Axel-exclusive $454 Nov 13, 2026

Route overview: Chicago to Montego Bay (MBJ) flight deals

2027-02-26 · one way · Axel-exclusive $185

2027-02-26 · one way · Axel-exclusive $237

2027-02-26 → 2027-02-27 · Axel-exclusive $417

2027-02-26 → 2027-02-27 · Axel-exclusive $464

2027-02-26 → 2027-02-28 · Axel-exclusive $397

2027-02-26 → 2027-02-28 · Axel-exclusive $443

2027-02-26 → 2027-03-01 · Axel-exclusive $407

2027-02-26 → 2027-03-01 · Axel-exclusive $454

2027-02-26 → 2027-03-02 · Axel-exclusive $407

2027-02-26 → 2027-03-02 · Axel-exclusive $454

2027-02-26 → 2027-03-04 · Axel-exclusive $407

2027-02-26 → 2027-03-04 · Axel-exclusive $454

2027-02-26 → 2027-03-05 · Axel-exclusive $407

2027-02-26 → 2027-03-05 · Axel-exclusive $454

2027-02-26 → 2027-03-06 · Axel-exclusive $429

2027-02-26 → 2027-03-06 · Axel-exclusive $475

2027-02-26 → 2027-03-08 · Axel-exclusive $407

2027-02-26 → 2027-03-08 · Axel-exclusive $454

2027-02-26 → 2027-03-09 · Axel-exclusive $407

2027-02-26 → 2027-03-09 · Axel-exclusive $454

2027-02-26 → 2027-03-10 · Axel-exclusive $407

2027-02-26 → 2027-03-10 · Axel-exclusive $454

2027-02-26 → 2027-03-12 · Axel-exclusive $407

2027-02-26 → 2027-03-12 · Axel-exclusive $454

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